Hydrochloric Acid → 3-Trifluoromethyl-4-phenyl-5-chloroisoxazole

HRID 477392Notes

Reaction equation

HRID 477392 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6](N)[O:5][N:4]=1.[ClH:17].[N+]([O-])([O-])=O.[Na+]>O>[F:1][C:2]([F:16])([F:15])[C:3]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6]([Cl:17])[O:5][N:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24268Sodium NitrateHCID 156138913-Trifluoromethyl-4-phenyl-5-aminoisoxazole

Product 1

HCID 143710873-Trifluoromethyl-4-phenyl-5-chloroisoxazoleYield 16.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 2.28 g (10.0 mmole) of 3-trifluoromethyl-4-phenyl-5-aminoisoxazole were added 20 ml of conc. HCl and 1.09 g (11. 0 mmole) of cuprous chloride and 4.2 ml of aqueous sodium nitrate (2.76 g, 40 mmole) was added dropwise to the reaction mixture, keeping the temperature at 20°-25° C. After addition, the temperature was raised to 40°-45° C. and the mixture was stirred for 1 hour. To the mixture was added 16 ml of water, extracted with methylene chloride, dried with anhydrous sodium sulfate, evaporated under reduced pressure. The residue was purified by chromatography on silica gel to give 0.5651 g of colorless liquid. This was distilled under reduced pressure to give 0.4193 g of the titled compound as colorless liquid, yield 16.9%, b.p. 80.0°-83.0° C./0.50 mmHg.

Workup

  1. additionwas added dropwise to the reaction mixture
  2. customat 20°-25° C
  3. additionAfter addition
  4. temperaturethe temperature was raised to 40°-45° C.
  5. extractionextracted with methylene chloride
  6. dry with materialdried with anhydrous sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-9a2637dc85144ca5a8eb66c8d453f4e8
Source dataset
uspto-grants-1989_12
Patent number
US04888044

Reaction notes

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